Ammonium Acetate → HCID 68867271, compound

HRID 733751Notes

Reaction equation

HRID 733751 reaction equation
[CH:1]([CH:3]([C:8]1[N:9]([CH3:18])[C:10]([CH3:17])=[CH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14])[C:4]([O:6][CH3:7])=[O:5])=O.C([O-])(=O)C.[NH4+:23]>CO>[NH2:23][CH:1]=[C:3]([C:8]1[N:9]([CH3:18])[C:10]([CH3:17])=[CH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 86615211HCID 86615211, compound

Product 1

HCID 68867271HCID 68867271, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-[1-formyl-2-(methyloxy)-2-oxoethyl]-1,5-dimethyl-1H-pyrrole-3-carboxylate (2.59 g), ammonium acetate (4.0 g) and methanol (50 ml) was heated under reflux for 4 hours. After cooling the solvent was evaporated and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with 2 further portions of ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and evaporated to afford the title compound 2.5 g, as a tautomeric mixture.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling the solvent
  4. customwas evaporated
  5. customthe residue was partitioned between ethyl acetate and water
  6. extractionThe aqueous phase was extracted with 2 further portions of ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-91a57487f40d4247ae9748b79f7e80a3
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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